Screening of yeast species for the stereo-selective reduction of bicyclo[2.2.2]octane-2,6-dione

Botes, Adriana L.; Harvig, Daniel; Dyk, M. S. Van; Sarvary, Ian; Frejd, Torbjörn; Katz, Mikael; Hahn‐Hägerdal, Bärbel; Gorwa-Grauslund, Marie-Françoise

doi:10.1039/b111064k

Cited by 20 publications

(15 citation statements)

References 28 publications

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“…As shown in Figure 15, Candida wickerhamii UOFS Y-0652 afforded mainly (+)-exo-isomer, and Cryptococcus albidus UOFS Y-2127 afforded (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octane-2-one((À)-endo-isomer) in 79% yield with >98% ee. 23 The reduction by baker's yeast also afforded the (1R,4S,6S)-isomer. Glucose was added as the co-substrate.…”

Section: Screening Of Microorganismmentioning

confidence: 98%

“…23,24 Yeast strains (327 strains) from more than 31 different genera were screened, and reducing activity was found in 80% of the screened yeasts (262 strains) containing 229 strains which gave (À)-endo isomer and 83 strains which gave exo isomers. As shown in Figure 15, Candida wickerhamii UOFS Y-0652 afforded mainly (+)-exo-isomer, and Cryptococcus albidus UOFS Y-2127 afforded (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octane-2-one((À)-endo-isomer) in 79% yield with >98% ee.…”

Section: Screening Of Microorganismmentioning

confidence: 99%

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Recent progress in biocatalysis for asymmetric oxidation and reduction

Matsuda

Yamanaka

Nakamura

2009

Tetrahedron: Asymmetry

365

163

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Section: Screening Of Microorganismmentioning

confidence: 98%

Section: Screening Of Microorganismmentioning

confidence: 99%

Recent progress in biocatalysis for asymmetric oxidation and reduction

Matsuda

Yamanaka

Nakamura

2009

Tetrahedron: Asymmetry

365

163

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“…1B). (Table 1B) Although S. cerevisiae has been and is the dominating yeast for the reduction of xenobiotic carbonyl compounds due to its reduction ability and easiness of use for organic chemists, other yeast species have been shown to generate another diastereomer [40,41] or the opposite enantiomer [28]. In other cases non-conventional yeasts have been able to reduce compounds not accepted by S. cerevisiae [42] or have been shown to contain reductases with different [43] or dual [44] co-factor dependency, these properties making the use of nonconventional yeast reductases attractive for the reduction of many xenobiotics.…”

Section: S Cerevisiae Dicarbonyl Reductasesmentioning

confidence: 99%

Strain engineering for stereoselective bioreduction of dicarbonyl compounds by yeast reductases

Johanson

Katz

Gorwa-Grauslund

2005

FEMS Yeast Research

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Pure chiral molecules are needed in the pharmaceutical and chemical industry as intermediates for the production of drugs or fine chemicals. Microorganisms represent an attractive alternative to chemical synthesis since they have the potential to generate single stereoisomers in high enantiomeric excess (ee). The baker's yeast Saccharomyces cerevisiae can notably reduce dicarbonyl compounds (in particular alpha- and beta-diketones and keto esters) to chiral alcohols with high ee. However, products are formed at a low rate. Moreover, large amounts of co-substrate are required for the regeneration of NADPH that is the preferred co-factor in almost all the known dicarbonyl reductions. Traditionally, better ee, reduction rate and product titre have been achieved via process engineering. The advent of recombinant DNA technology provides an alternative strategy to improve productivity and yield by strain engineering. This review discusses two aspects of strain engineering: (i) the generation of strains with higher reductase activity towards dicarbonyl compounds and (ii) the optimisation of co-substrate utilisation for NADPH cofactor regeneration.

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“…In the new protocol, BODOLs 3a-l were synthesized by the addition of the corresponding Grignard reagent to hydroxyketone 1 [25][26][27] in ether solution without prior protection ( Table 1). The reaction was performed at 25°C using the organomagnesium In the synthesis of the substituted BODOLs, 1 equiv of the reagent was added upon which a precipitate was formed, which dissolved after the addition of another 1.5 equiv.…”

Section: Resultsmentioning

confidence: 99%